Methylamine → HCID 18625842, compound

HRID 1860030Notes

Reaction equation

HRID 1860030 reaction equation
[CH3:1][NH2:2].[CH2:3]([CH:7]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23]OS(C)(=O)=O)=[CH:16][CH:15]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:5][CH3:6]>CO.C1(C)C=CC=CC=1>[CH2:3]([CH:7]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][NH:2][CH3:1])=[CH:16][CH:15]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 18625784HCID 18625784, compound

Product 1

HCID 18625842HCID 18625842, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of methylamine in methanol (40%, 5.0 ml) was added to a solution of ethyl 2-butyl-3-[4-(3-methansulfonyloxypropoxy)phenyl]propionate (500 mg), which is the product of Reference example 21 (c) in toluene (10 ml). The mixture was stirred at 90° C. for 2 days. The reaction mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water and the layers were separated. The ethyl acetate solution was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified via chromatography on a silica gel column using dichloromethane/methanol=5/1 as the eluant to afford the title compound (389 mg) as a pale yellow oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. customthe layers were separated
  4. dry with materialThe ethyl acetate solution was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified via chromatography on a silica gel column

Sources & evidence

ORD record
ord-928a9ff6adbe460589b1445945f4d22c
Source dataset
uspto-grants-2003_03
Patent number
US06528525B1

Reaction notes

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